# Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Chuan-Ming Jin' _publ_contact_author_email JINCM1999@YAHOO.COM _publ_section_title ; In situ reduction from CuX2 (X = Br, Cl) to Cu(I) halide clusters based on ligand bis(2-methylimidazo-1-yl)methane ; loop_ _publ_author_name 'Chuan-Ming Jin' 'Xianggao Meng' 'Ming-Xia Yao' 'Zhu Zhu' # Attachment '688402.CIF' data_jcm5b _database_code_depnum_ccdc_archive 'CCDC 688402' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H10 Br Cu N4' _chemical_formula_sum 'C9 H10 Br Cu N4' _chemical_formula_weight 317.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Cmca _symmetry_space_group_name_Hall '-C 2bc 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' '-x, y+1/2, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z+1/2' '-x+1/2, y+1, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' 'x, -y-1/2, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y, -z-1/2' 'x+1/2, -y, z-1/2' '-x+1/2, y+1/2, z' _cell_length_a 21.500(17) _cell_length_b 27.568(17) _cell_length_c 7.428(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4402(5) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.917 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2496 _exptl_absorpt_coefficient_mu 5.585 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.5304 _exptl_absorpt_correction_T_max 0.6051 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10297 _diffrn_reflns_av_R_equivalents 0.0688 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2007 _reflns_number_gt 1122 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'SMART, (Bruker, 2001)' _computing_cell_refinement 'SAINT+ (Bruker, 2001)' _computing_data_reduction SAINT+ _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1595P)^2^+16.0300P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef 0.0050(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2007 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1361 _refine_ls_R_factor_gt 0.0917 _refine_ls_wR_factor_ref 0.2718 _refine_ls_wR_factor_gt 0.2555 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.43781(7) 0.5000 0.0000 0.0426(7) Uani 1 2 d S . . Cu2 Cu 0.31187(13) 0.25050(9) 0.0111(3) 0.0513(8) Uani 0.50 1 d P . . Br1 Br 0.2500 0.30163(8) 0.2500 0.0714(8) Uani 1 2 d S . . Br2 Br 0.5000 0.44817(6) 0.21613(18) 0.0424(6) Uani 1 2 d S . . N1 N 0.3850(4) 0.4579(3) -0.1647(12) 0.044(2) Uani 1 1 d . . . C2 C 0.3408(5) 0.4231(4) -0.4007(13) 0.048(3) Uani 1 1 d . . . H2A H 0.3329 0.4140 -0.5191 0.057 Uiso 1 1 calc R . . N3 N 0.3648(4) 0.2054(3) 0.1718(12) 0.041(2) Uani 0.50 1 d P . 1 C6A C 0.3648(4) 0.2054(3) 0.1718(12) 0.041(2) Uani 0.50 1 d P . 2 C7 C 0.4120(5) 0.1757(5) 0.4027(13) 0.049(3) Uani 1 1 d . . . C1 C 0.3888(5) 0.4513(4) -0.3362(16) 0.053(3) Uani 1 1 d . . . H1A H 0.4222 0.4639 -0.4080 0.063 Uiso 1 1 d R . . N2 N 0.3081(5) 0.4119(3) -0.2522(9) 0.046(3) Uani 1 1 d . . . C3 C 0.3352(5) 0.4329(4) -0.1106(13) 0.041(2) Uani 1 1 d . . . C4 C 0.2500 0.3824(6) -0.2500 0.052(5) Uani 1 2 d S . . H4A H 0.2504 0.3618 -0.1458 0.062 Uiso 0.50 1 d PR . . C5 C 0.3127(5) 0.4290(5) 0.0814(12) 0.059(3) Uani 1 1 d . . . H5A H 0.2763 0.4087 0.0861 0.088 Uiso 1 1 d R . . H5B H 0.3447 0.4152 0.1557 0.088 Uiso 1 1 d R . . H5C H 0.3025 0.4608 0.1245 0.088 Uiso 1 1 d R . . C6 C 0.3634(4) 0.2036(3) 0.3439(13) 0.048(3) Uani 0.50 1 d P . 1 H6A H 0.3329 0.2190 0.4189 0.057 Uiso 1 1 d R . 1 N3A N 0.3634(4) 0.2036(3) 0.3439(13) 0.048(3) Uani 0.50 1 d P . 2 N4 N 0.4415(5) 0.1620(3) 0.2549(9) 0.045(2) Uani 1 1 d . . . C8 C 0.4131(5) 0.1794(4) 0.1099(13) 0.047(3) Uani 1 1 d . . . C9 C 0.5000 0.1335(6) 0.254(2) 0.054(5) Uani 1 2 d S . . H9A H 0.5000 0.1127 0.1501 0.064 Uiso 1 2 d SR . . H9B H 0.5000 0.1131 0.3586 0.064 Uiso 1 2 d SR . . C10 C 0.4389(10) 0.1792(10) -0.070(3) 0.066(7) Uani 0.50 1 d P . 1 H10A H 0.4731 0.1569 -0.0772 0.099 Uiso 0.50 1 d PR . 1 H10B H 0.4076 0.1700 -0.1559 0.099 Uiso 0.50 1 d PR . 1 H10C H 0.4533 0.2113 -0.0968 0.099 Uiso 0.50 1 d PR . 1 C10A C 0.4354(11) 0.1744(11) 0.586(3) 0.080(9) Uani 0.50 1 d P . 2 H10D H 0.4698 0.1523 0.5945 0.120 Uiso 0.50 1 d PR . 2 H10E H 0.4491 0.2066 0.6159 0.120 Uiso 0.50 1 d PR . 2 H10F H 0.4031 0.1646 0.6672 0.120 Uiso 0.50 1 d PR . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0269(10) 0.0442(12) 0.0568(11) -0.0089(8) 0.000 0.000 Cu2 0.0367(15) 0.0571(19) 0.0600(16) 0.0070(15) 0.0046(10) 0.0011(12) Br1 0.0504(13) 0.0497(14) 0.1141(18) 0.000 0.0315(9) 0.000 Br2 0.0467(10) 0.0458(11) 0.0346(8) 0.0089(6) 0.000 0.000 N1 0.032(5) 0.039(5) 0.061(5) 0.007(4) 0.005(4) -0.007(4) C2 0.045(6) 0.067(7) 0.032(5) 0.007(5) -0.004(4) 0.016(6) N3 0.034(5) 0.037(6) 0.051(5) 0.001(4) 0.009(4) 0.001(4) C6A 0.034(5) 0.037(6) 0.051(5) 0.001(4) 0.009(4) 0.001(4) C7 0.036(6) 0.076(8) 0.036(5) -0.003(5) -0.002(4) -0.004(6) C1 0.043(6) 0.047(7) 0.067(7) 0.012(5) -0.009(6) -0.008(5) N2 0.053(7) 0.046(6) 0.039(4) 0.005(3) -0.006(3) 0.004(6) C3 0.037(6) 0.051(7) 0.036(5) 0.007(4) 0.003(4) 0.005(5) C4 0.039(11) 0.032(11) 0.084(12) 0.000 -0.009(7) 0.000 C5 0.049(6) 0.090(9) 0.038(5) -0.002(5) 0.006(5) -0.022(6) C6 0.035(5) 0.049(6) 0.059(6) -0.009(5) 0.002(4) 0.010(4) N3A 0.035(5) 0.049(6) 0.059(6) -0.009(5) 0.002(4) 0.010(4) N4 0.050(7) 0.042(6) 0.042(5) -0.003(3) 0.008(3) -0.001(6) C8 0.047(7) 0.055(7) 0.038(5) 0.001(5) 0.002(5) 0.004(6) C9 0.054(13) 0.035(11) 0.072(11) 0.001(7) 0.000 0.000 C10 0.048(14) 0.11(2) 0.043(11) -0.018(13) -0.018(10) 0.037(14) C10A 0.045(14) 0.14(3) 0.059(13) 0.053(16) 0.020(11) 0.040(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.034(9) . ? Cu1 N1 2.034(9) 4_565 ? Cu1 Br2 2.5311(17) . ? Cu1 Br2 2.5311(17) 9_665 ? Cu1 Cu1 2.674(4) 9_665 ? Cu2 N3 2.066(9) . ? Cu2 N3A 2.091(9) 11_565 ? Cu2 C6 2.091(9) 11_565 ? Cu2 Br1 2.628(3) . ? Cu2 Cu2 2.665(6) 13 ? Cu2 Br1 2.756(3) 13 ? Br1 Cu2 2.628(3) 7_545 ? Br1 Cu2 2.756(3) 13 ? Br1 Cu2 2.756(3) 11_566 ? Br2 Cu1 2.5311(17) 9_665 ? N1 C1 1.290(15) . ? N1 C3 1.334(12) . ? C2 N2 1.343(12) . ? C2 C1 1.379(14) . ? N3 C6 1.279(14) . ? N3 C8 1.342(13) . ? C7 N4 1.323(12) . ? C7 C6 1.370(13) . ? C7 C10A 1.45(2) . ? N2 C3 1.334(12) . ? N2 C4 1.491(13) . ? C3 C5 1.510(12) . ? C4 N2 1.491(13) 7_544 ? C6 Cu2 2.091(9) 11_566 ? N4 C8 1.329(13) . ? N4 C9 1.482(13) . ? C8 C10 1.45(2) . ? C9 N4 1.482(13) 12_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 112.1(5) . 4_565 ? N1 Cu1 Br2 110.7(2) . . ? N1 Cu1 Br2 103.7(2) 4_565 . ? N1 Cu1 Br2 103.7(2) . 9_665 ? N1 Cu1 Br2 110.7(2) 4_565 9_665 ? Br2 Cu1 Br2 116.22(8) . 9_665 ? N1 Cu1 Cu1 124.0(2) . 9_665 ? N1 Cu1 Cu1 124.0(2) 4_565 9_665 ? Br2 Cu1 Cu1 58.11(4) . 9_665 ? Br2 Cu1 Cu1 58.11(4) 9_665 9_665 ? N3 Cu2 N3A 114.6(4) . 11_565 ? N3 Cu2 C6 114.6(4) . 11_565 ? N3A Cu2 C6 0.0(7) 11_565 11_565 ? N3 Cu2 Br1 102.2(3) . . ? N3A Cu2 Br1 110.1(3) 11_565 . ? C6 Cu2 Br1 110.1(3) 11_565 . ? N3 Cu2 Cu2 125.4(3) . 13 ? N3A Cu2 Cu2 119.9(3) 11_565 13 ? C6 Cu2 Cu2 119.9(3) 11_565 13 ? Br1 Cu2 Cu2 62.75(10) . 13 ? N3 Cu2 Br1 111.0(3) . 13 ? N3A Cu2 Br1 98.8(3) 11_565 13 ? C6 Cu2 Br1 98.8(3) 11_565 13 ? Br1 Cu2 Br1 120.71(12) . 13 ? Cu2 Cu2 Br1 57.96(10) 13 13 ? Cu2 Br1 Cu2 115.12(14) . 7_545 ? Cu2 Br1 Cu2 59.29(12) . 13 ? Cu2 Br1 Cu2 87.20(9) 7_545 13 ? Cu2 Br1 Cu2 87.20(9) . 11_566 ? Cu2 Br1 Cu2 59.29(12) 7_545 11_566 ? Cu2 Br1 Cu2 117.14(13) 13 11_566 ? Cu1 Br2 Cu1 63.78(8) . 9_665 ? C1 N1 C3 106.0(8) . . ? C1 N1 Cu1 129.7(6) . . ? C3 N1 Cu1 124.2(7) . . ? N2 C2 C1 103.6(9) . . ? C6 N3 C8 109.9(8) . . ? C6 N3 Cu2 126.0(6) . . ? C8 N3 Cu2 123.3(7) . . ? N4 C7 C6 105.2(9) . . ? N4 C7 C10A 127.2(12) . . ? C6 C7 C10A 125.3(13) . . ? N1 C1 C2 112.0(9) . . ? C3 N2 C2 108.6(10) . . ? C3 N2 C4 126.4(7) . . ? C2 N2 C4 124.9(7) . . ? N2 C3 N1 109.7(9) . . ? N2 C3 C5 125.0(9) . . ? N1 C3 C5 125.4(9) . . ? N2 C4 N2 113.9(13) . 7_544 ? N3 C6 C7 108.8(8) . . ? N3 C6 Cu2 125.6(7) . 11_566 ? C7 C6 Cu2 123.7(7) . 11_566 ? C7 N4 C8 110.4(10) . . ? C7 N4 C9 124.2(10) . . ? C8 N4 C9 125.3(9) . . ? N4 C8 N3 105.7(9) . . ? N4 C8 C10 124.8(12) . . ? N3 C8 C10 128.0(13) . . ? N4 C9 N4 116.0(13) . 12_655 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.519 _refine_diff_density_min -3.655 _refine_diff_density_rms 0.288 # Attachment '688404.cif' data_y2440 _database_code_depnum_ccdc_archive 'CCDC 688404' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H12 Cl2 Cu2 N4' _chemical_formula_weight 374.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I4(1)/acd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+1/4, x+3/4, z+1/4' 'y+1/4, -x+1/4, z+3/4' '-x+1/2, y, -z' 'x, -y, -z+1/2' 'y+1/4, x+3/4, -z+3/4' '-y+1/4, -x+1/4, -z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+3/4, x+5/4, z+3/4' 'y+3/4, -x+3/4, z+5/4' '-x+1, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1' 'y+3/4, x+5/4, -z+5/4' '-y+3/4, -x+3/4, -z+3/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-1/4, -x-3/4, -z-1/4' '-y-1/4, x-1/4, -z-3/4' 'x-1/2, -y, z' '-x, y, z-1/2' '-y-1/4, -x-3/4, z-3/4' 'y-1/4, x-1/4, z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y+1/4, -x-1/4, -z+1/4' '-y+1/4, x+1/4, -z-1/4' 'x, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' '-y+1/4, -x-1/4, z-1/4' 'y+1/4, x+1/4, z+1/4' _cell_length_a 12.9571(2) _cell_length_b 12.9571(2) _cell_length_c 30.9700(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5199.44(16) _cell_formula_units_Z 16 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 23697 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.912 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2976 _exptl_absorpt_coefficient_mu 3.664 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5747 _exptl_absorpt_correction_T_max 0.6887 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 33662 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1278 _reflns_number_gt 1058 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto Version 3.0 (Rigaku 2004)' _computing_cell_refinement 'Rapid Auto Version 3.0 (Rigaku 2004)' _computing_data_reduction 'Rapid Auto Version 3.0 (Rigaku 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1560P)^2^+8.2000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00024(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1278 _refine_ls_number_parameters 80 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.2025 _refine_ls_wR_factor_gt 0.1892 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.53388(8) -0.13305(5) 0.58880(3) 0.0693(5) Uani 1 1 d . . . Cl1 Cl 0.36004(9) -0.23832(9) 0.57623(4) 0.0433(4) Uani 1 1 d . . . N1 N 0.4930(4) 0.0055(4) 0.57597(13) 0.0503(10) Uani 1 1 d . . . N2 N 0.4801(3) 0.1600(3) 0.54855(14) 0.0455(9) Uani 1 1 d . . . C1 C 0.4018(5) 0.0526(5) 0.59045(19) 0.0596(14) Uani 1 1 d . . . H1 H 0.3535 0.0218 0.6096 0.071 Uiso 1 1 calc R . . C2 C 0.3927(4) 0.1453(5) 0.57380(19) 0.0594(14) Uani 1 1 d . . . H2 H 0.3377 0.1926 0.5781 0.071 Uiso 1 1 calc R . . C3 C 0.5376(4) 0.0740(4) 0.55121(15) 0.0420(10) Uani 1 1 d . . . C4 C 0.5000 0.2500 0.5224(2) 0.0561(19) Uani 1 2 d S . . H4A H 0.5603 0.2367 0.5036 0.067 Uiso 0.50 1 calc PR . . H4B H 0.4397 0.2633 0.5036 0.067 Uiso 0.50 1 calc PR . . C5 C 0.6367(4) 0.0585(4) 0.52907(17) 0.0549(13) Uani 1 1 d . . . H5A H 0.6589 -0.0133 0.5326 0.066 Uiso 1 1 calc R . . H5B H 0.6887 0.1046 0.5416 0.066 Uiso 1 1 calc R . . H5C H 0.6286 0.0738 0.4983 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.1027(8) 0.0347(5) 0.0705(7) 0.0006(3) -0.0135(4) 0.0076(3) Cl1 0.0395(7) 0.0443(7) 0.0462(7) 0.0041(4) -0.0001(4) -0.0016(4) N1 0.059(3) 0.037(2) 0.054(2) 0.0008(17) -0.0038(19) -0.0052(19) N2 0.052(2) 0.037(2) 0.048(2) 0.0009(17) -0.0009(17) 0.0019(17) C1 0.051(3) 0.061(4) 0.066(3) -0.002(3) 0.016(2) -0.006(3) C2 0.045(3) 0.065(4) 0.068(3) -0.008(3) 0.006(2) 0.008(2) C3 0.044(2) 0.037(2) 0.044(2) -0.0018(18) -0.0007(18) 0.0001(18) C4 0.090(6) 0.034(4) 0.044(3) 0.000 0.000 0.012(4) C5 0.052(3) 0.056(3) 0.057(3) -0.010(2) 0.006(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.913(5) . ? Cu1 Cl1 2.1952(14) 10_544 ? Cu1 Cl1 2.6619(16) . ? Cu1 Cu1 2.7100(16) 15_535 ? Cu1 Cl1 2.7132(14) 8_556 ? Cl1 Cu1 2.1951(14) 10_544 ? Cl1 Cu1 2.7132(14) 8_556 ? N1 C3 1.307(6) . ? N1 C1 1.404(8) . ? N2 C3 1.344(7) . ? N2 C2 1.389(7) . ? N2 C4 1.443(6) . ? C1 C2 1.312(9) . ? C1 H1 0.9500 . ? C2 H2 0.9500 . ? C3 C5 1.469(7) . ? C4 N2 1.443(6) 10_554 ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 Cl1 148.08(16) . 10_544 ? N1 Cu1 Cl1 102.49(15) . . ? Cl1 Cu1 Cl1 96.59(5) 10_544 . ? N1 Cu1 Cu1 130.87(13) . 15_535 ? Cl1 Cu1 Cu1 66.20(5) 10_544 15_535 ? Cl1 Cu1 Cu1 104.69(3) . 15_535 ? N1 Cu1 Cl1 92.18(14) . 8_556 ? Cl1 Cu1 Cl1 113.06(5) 10_544 8_556 ? Cl1 Cu1 Cl1 90.80(5) . 8_556 ? Cu1 Cu1 Cl1 47.75(4) 15_535 8_556 ? Cu1 Cl1 Cu1 80.40(5) 10_544 . ? Cu1 Cl1 Cu1 66.05(5) 10_544 8_556 ? Cu1 Cl1 Cu1 82.92(5) . 8_556 ? C3 N1 C1 105.3(5) . . ? C3 N1 Cu1 129.5(4) . . ? C1 N1 Cu1 125.1(4) . . ? C3 N2 C2 107.6(4) . . ? C3 N2 C4 127.3(4) . . ? C2 N2 C4 124.9(4) . . ? C2 C1 N1 110.4(5) . . ? C2 C1 H1 124.8 . . ? N1 C1 H1 124.8 . . ? C1 C2 N2 105.9(5) . . ? C1 C2 H2 127.1 . . ? N2 C2 H2 127.1 . . ? N1 C3 N2 110.8(4) . . ? N1 C3 C5 124.6(5) . . ? N2 C3 C5 124.7(4) . . ? N2 C4 N2 111.6(6) 10_554 . ? N2 C4 H4A 109.3 10_554 . ? N2 C4 H4A 109.3 . . ? N2 C4 H4B 109.3 10_554 . ? N2 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 Cl1 Cu1 174.67(14) . . . 10_544 ? Cl1 Cu1 Cl1 Cu1 20.41(8) 10_544 . . 10_544 ? Cu1 Cu1 Cl1 Cu1 -46.66(7) 15_535 . . 10_544 ? Cl1 Cu1 Cl1 Cu1 -92.91(5) 8_556 . . 10_544 ? N1 Cu1 Cl1 Cu1 -118.52(14) . . . 8_556 ? Cl1 Cu1 Cl1 Cu1 87.22(6) 10_544 . . 8_556 ? Cu1 Cu1 Cl1 Cu1 20.15(7) 15_535 . . 8_556 ? Cl1 Cu1 Cl1 Cu1 -26.11(6) 8_556 . . 8_556 ? Cl1 Cu1 N1 C3 -6.1(6) 10_544 . . . ? Cl1 Cu1 N1 C3 -131.4(4) . . . . ? Cu1 Cu1 N1 C3 106.2(4) 15_535 . . . ? Cl1 Cu1 N1 C3 137.3(4) 8_556 . . . ? Cl1 Cu1 N1 C1 170.1(3) 10_544 . . . ? Cl1 Cu1 N1 C1 44.8(4) . . . . ? Cu1 Cu1 N1 C1 -77.6(5) 15_535 . . . ? Cl1 Cu1 N1 C1 -46.5(4) 8_556 . . . ? C3 N1 C1 C2 1.2(7) . . . . ? Cu1 N1 C1 C2 -175.7(4) . . . . ? N1 C1 C2 N2 -1.0(7) . . . . ? C3 N2 C2 C1 0.4(6) . . . . ? C4 N2 C2 C1 176.8(5) . . . . ? C1 N1 C3 N2 -1.0(6) . . . . ? Cu1 N1 C3 N2 175.8(3) . . . . ? C1 N1 C3 C5 179.4(5) . . . . ? Cu1 N1 C3 C5 -3.8(8) . . . . ? C2 N2 C3 N1 0.4(6) . . . . ? C4 N2 C3 N1 -175.9(5) . . . . ? C2 N2 C3 C5 -180.0(5) . . . . ? C4 N2 C3 C5 3.7(8) . . . . ? C3 N2 C4 N2 -115.1(5) . . . 10_554 ? C2 N2 C4 N2 69.2(5) . . . 10_554 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.751 _refine_diff_density_min -1.130 _refine_diff_density_rms 0.118